Acta Cryst. (2009). E65, o2147 [ doi:10.1107/S1600536809031419 ]
In the title compound, C14H13N3O3, the pyrazoline ring assumes an envelope conformation with the furanyl-bearing C atom at the flap position. The dihedral angle between the furan and nitrobenzene rings is 84.40 (9)°. Weak intermolecular C-H
O hydrogen bonding is present in the crystal structure.
3-Nitrophenylhydrazine (1 mmol, 0.153 g) was dissolved in anhydrous ethanol (15 ml). The mixture was stirred for several min at 351 K, furylideneacetone (1 mmol, 0.136 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from methanol, bronze single crystals of (I) were obtained after 3 d.
All H atoms were positioned geometrically and refined as riding with C—H = 0.93 (aromatic), 0.97 (methylene), 0.98 (methine) and 0.96 Å (methyl), with Uiso(H)=1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
![[Figure 1]](./xu2580fig1thm.gif)
| Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. |
![[Figure 2]](./xu2580fig2thm.gif)
| Fig. 2. Packing of (I), showing the intermolecular hydrogen bonds as dashed lines. |
| C14H13N3O3 | Z = 2 |
| Mr = 271.27 | F(000) = 284 |
| Triclinic, P1 | Dx = 1.362 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 6.2089 (2) Å | Cell parameters from 1598 reflections |
| b = 7.8581 (3) Å | θ = 3.5–24.6° |
| c = 14.3800 (4) Å | µ = 0.10 mm−1 |
| α = 105.764 (2)° | T = 296 K |
| β = 97.054 (2)° | Block, bronze |
| γ = 96.944 (2)° | 0.31 × 0.15 × 0.10 mm |
| V = 661.31 (4) Å3 |
| Bruker SMART CCD area-detector diffractometer | 1778 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.036 |
| graphite | θmax = 26.0°, θmin = 3.5° |
| ω scans | h = −7→7 |
| 9707 measured reflections | k = −8→9 |
| 2590 independent reflections | l = −17→17 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.121 | H-atom parameters constrained |
| S = 1.10 | w = 1/[σ2(Fo2) + (0.0608P)2] where P = (Fo2 + 2Fc2)/3 |
| 2590 reflections | (Δ/σ)max = 0.003 |
| 181 parameters | Δρmax = 0.14 e Å−3 |
| 0 restraints | Δρmin = −0.20 e Å−3 |
| C14H13N3O3 | γ = 96.944 (2)° |
| Mr = 271.27 | V = 661.31 (4) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 6.2089 (2) Å | Mo Kα radiation |
| b = 7.8581 (3) Å | µ = 0.10 mm−1 |
| c = 14.3800 (4) Å | T = 296 K |
| α = 105.764 (2)° | 0.31 × 0.15 × 0.10 mm |
| β = 97.054 (2)° |
| Bruker SMART CCD area-detector diffractometer | 1778 reflections with I > 2σ(I) |
| 9707 measured reflections | Rint = 0.036 |
| 2590 independent reflections | θmax = 26.0° |
| R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
| wR(F2) = 0.121 | Δρmax = 0.14 e Å−3 |
| S = 1.10 | Δρmin = −0.20 e Å−3 |
| 2590 reflections | Absolute structure: ? |
| 181 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| O | 0.36743 (18) | 0.34679 (15) | 0.90208 (8) | 0.0586 (3) | |
| N1 | 0.1661 (2) | 0.62239 (17) | 0.78604 (10) | 0.0496 (4) | |
| N2 | 0.2000 (2) | 0.45740 (16) | 0.72794 (10) | 0.0491 (4) | |
| C9 | 0.3755 (2) | 0.4521 (2) | 0.67745 (11) | 0.0429 (4) | |
| C14 | 0.5059 (2) | 0.6102 (2) | 0.67820 (11) | 0.0460 (4) | |
| H14A | 0.4772 | 0.7211 | 0.7132 | 0.055* | |
| C7 | 0.0168 (3) | 0.5942 (2) | 0.83623 (13) | 0.0534 (4) | |
| C10 | 0.4224 (3) | 0.2892 (2) | 0.62195 (12) | 0.0546 (4) | |
| H10A | 0.3347 | 0.1826 | 0.6191 | 0.066* | |
| C4 | 0.2531 (2) | 0.2318 (2) | 0.81601 (12) | 0.0477 (4) | |
| C13 | 0.6784 (2) | 0.5987 (2) | 0.62600 (12) | 0.0514 (4) | |
| N3 | 0.8105 (2) | 0.7665 (2) | 0.62761 (12) | 0.0680 (5) | |
| O1 | 0.9707 (2) | 0.7615 (2) | 0.58611 (11) | 0.0934 (5) | |
| C5 | 0.0941 (2) | 0.3072 (2) | 0.75855 (12) | 0.0508 (4) | |
| H5A | 0.0138 | 0.2126 | 0.7010 | 0.061* | |
| C12 | 0.7298 (3) | 0.4395 (3) | 0.57272 (12) | 0.0611 (5) | |
| H12A | 0.8487 | 0.4365 | 0.5391 | 0.073* | |
| C6 | −0.0684 (3) | 0.4007 (3) | 0.81836 (14) | 0.0615 (5) | |
| H6A | −0.2166 | 0.3686 | 0.7817 | 0.074* | |
| H6B | −0.0677 | 0.3706 | 0.8795 | 0.074* | |
| C1 | 0.4967 (3) | 0.2476 (3) | 0.94299 (14) | 0.0607 (5) | |
| H1B | 0.5924 | 0.2920 | 1.0022 | 0.073* | |
| O2 | 0.7571 (3) | 0.9062 (2) | 0.67000 (14) | 0.1046 (6) | |
| C11 | 0.5976 (3) | 0.2848 (3) | 0.57136 (13) | 0.0642 (5) | |
| H11A | 0.6270 | 0.1748 | 0.5355 | 0.077* | |
| C3 | 0.3090 (3) | 0.0707 (2) | 0.80439 (14) | 0.0660 (5) | |
| H3A | 0.2550 | −0.0308 | 0.7518 | 0.079* | |
| C2 | 0.4665 (3) | 0.0818 (3) | 0.88708 (14) | 0.0673 (5) | |
| H2A | 0.5350 | −0.0108 | 0.8992 | 0.081* | |
| C8 | −0.0654 (3) | 0.7433 (3) | 0.90245 (15) | 0.0793 (6) | |
| H8A | 0.0141 | 0.8556 | 0.9019 | 0.119* | |
| H8B | −0.0444 | 0.7329 | 0.9678 | 0.119* | |
| H8C | −0.2191 | 0.7381 | 0.8806 | 0.119* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O | 0.0577 (7) | 0.0535 (7) | 0.0622 (8) | 0.0133 (5) | 0.0000 (6) | 0.0156 (6) |
| N1 | 0.0513 (8) | 0.0481 (8) | 0.0555 (8) | 0.0152 (6) | 0.0159 (6) | 0.0190 (7) |
| N2 | 0.0507 (7) | 0.0414 (7) | 0.0613 (9) | 0.0090 (6) | 0.0178 (6) | 0.0206 (7) |
| C9 | 0.0443 (8) | 0.0457 (9) | 0.0417 (9) | 0.0103 (7) | 0.0050 (7) | 0.0172 (7) |
| C14 | 0.0459 (8) | 0.0467 (9) | 0.0464 (9) | 0.0077 (7) | 0.0087 (7) | 0.0147 (7) |
| C7 | 0.0454 (8) | 0.0673 (11) | 0.0568 (10) | 0.0186 (8) | 0.0109 (8) | 0.0284 (9) |
| C10 | 0.0639 (10) | 0.0459 (10) | 0.0528 (10) | 0.0079 (8) | 0.0105 (8) | 0.0125 (8) |
| C4 | 0.0474 (8) | 0.0414 (9) | 0.0544 (10) | 0.0009 (7) | 0.0061 (7) | 0.0179 (8) |
| C13 | 0.0452 (9) | 0.0591 (10) | 0.0501 (10) | 0.0017 (8) | 0.0074 (7) | 0.0191 (8) |
| N3 | 0.0584 (9) | 0.0749 (12) | 0.0685 (10) | −0.0040 (8) | 0.0163 (8) | 0.0210 (9) |
| O1 | 0.0729 (9) | 0.1114 (12) | 0.0966 (11) | −0.0083 (8) | 0.0418 (8) | 0.0290 (9) |
| C5 | 0.0440 (8) | 0.0488 (9) | 0.0621 (10) | −0.0003 (7) | 0.0046 (7) | 0.0256 (8) |
| C12 | 0.0591 (10) | 0.0759 (13) | 0.0516 (11) | 0.0182 (9) | 0.0200 (8) | 0.0159 (9) |
| C6 | 0.0403 (8) | 0.0813 (13) | 0.0765 (12) | 0.0102 (8) | 0.0121 (8) | 0.0440 (11) |
| C1 | 0.0531 (10) | 0.0751 (13) | 0.0613 (11) | 0.0207 (9) | 0.0076 (8) | 0.0285 (10) |
| O2 | 0.0990 (12) | 0.0602 (9) | 0.1522 (16) | −0.0069 (8) | 0.0581 (11) | 0.0187 (10) |
| C11 | 0.0777 (12) | 0.0602 (11) | 0.0550 (11) | 0.0230 (10) | 0.0176 (10) | 0.0093 (9) |
| C3 | 0.0813 (13) | 0.0457 (10) | 0.0690 (13) | 0.0129 (9) | 0.0027 (10) | 0.0164 (9) |
| C2 | 0.0761 (12) | 0.0621 (13) | 0.0761 (13) | 0.0288 (10) | 0.0118 (10) | 0.0333 (11) |
| C8 | 0.0778 (13) | 0.0996 (16) | 0.0771 (14) | 0.0422 (12) | 0.0352 (11) | 0.0316 (12) |
| O—C4 | 1.3689 (18) | N3—O2 | 1.208 (2) |
| O—C1 | 1.372 (2) | N3—O1 | 1.2209 (19) |
| N1—C7 | 1.277 (2) | C5—C6 | 1.532 (2) |
| N1—N2 | 1.3940 (18) | C5—H5A | 0.9800 |
| N2—C9 | 1.3803 (19) | C12—C11 | 1.376 (3) |
| N2—C5 | 1.4784 (19) | C12—H12A | 0.9300 |
| C9—C14 | 1.396 (2) | C6—H6A | 0.9700 |
| C9—C10 | 1.397 (2) | C6—H6B | 0.9700 |
| C14—C13 | 1.379 (2) | C1—C2 | 1.309 (2) |
| C14—H14A | 0.9300 | C1—H1B | 0.9300 |
| C7—C8 | 1.482 (2) | C11—H11A | 0.9300 |
| C7—C6 | 1.489 (3) | C3—C2 | 1.420 (2) |
| C10—C11 | 1.380 (2) | C3—H3A | 0.9300 |
| C10—H10A | 0.9300 | C2—H2A | 0.9300 |
| C4—C3 | 1.325 (2) | C8—H8A | 0.9600 |
| C4—C5 | 1.488 (2) | C8—H8B | 0.9600 |
| C13—C12 | 1.375 (2) | C8—H8C | 0.9600 |
| C13—N3 | 1.459 (2) | ||
| C4—O—C1 | 105.97 (13) | C4—C5—H5A | 110.0 |
| C7—N1—N2 | 108.34 (13) | C6—C5—H5A | 110.0 |
| C9—N2—N1 | 118.80 (12) | C13—C12—C11 | 117.03 (16) |
| C9—N2—C5 | 125.31 (13) | C13—C12—H12A | 121.5 |
| N1—N2—C5 | 111.64 (12) | C11—C12—H12A | 121.5 |
| N2—C9—C14 | 120.55 (14) | C7—C6—C5 | 103.00 (13) |
| N2—C9—C10 | 120.96 (14) | C7—C6—H6A | 111.2 |
| C14—C9—C10 | 118.47 (14) | C5—C6—H6A | 111.2 |
| C13—C14—C9 | 118.59 (15) | C7—C6—H6B | 111.2 |
| C13—C14—H14A | 120.7 | C5—C6—H6B | 111.2 |
| C9—C14—H14A | 120.7 | H6A—C6—H6B | 109.1 |
| N1—C7—C8 | 121.87 (16) | C2—C1—O | 110.60 (15) |
| N1—C7—C6 | 113.46 (15) | C2—C1—H1B | 124.7 |
| C8—C7—C6 | 124.64 (16) | O—C1—H1B | 124.7 |
| C11—C10—C9 | 120.67 (16) | C12—C11—C10 | 121.50 (17) |
| C11—C10—H10A | 119.7 | C12—C11—H11A | 119.3 |
| C9—C10—H10A | 119.7 | C10—C11—H11A | 119.3 |
| C3—C4—O | 109.50 (15) | C4—C3—C2 | 107.27 (16) |
| C3—C4—C5 | 134.10 (17) | C4—C3—H3A | 126.4 |
| O—C4—C5 | 116.37 (14) | C2—C3—H3A | 126.4 |
| C12—C13—C14 | 123.72 (16) | C1—C2—C3 | 106.65 (16) |
| C12—C13—N3 | 119.04 (15) | C1—C2—H2A | 126.7 |
| C14—C13—N3 | 117.24 (15) | C3—C2—H2A | 126.7 |
| O2—N3—O1 | 122.13 (17) | C7—C8—H8A | 109.5 |
| O2—N3—C13 | 118.76 (15) | C7—C8—H8B | 109.5 |
| O1—N3—C13 | 119.11 (17) | H8A—C8—H8B | 109.5 |
| N2—C5—C4 | 112.93 (12) | C7—C8—H8C | 109.5 |
| N2—C5—C6 | 100.18 (13) | H8A—C8—H8C | 109.5 |
| C4—C5—C6 | 113.50 (14) | H8B—C8—H8C | 109.5 |
| N2—C5—H5A | 110.0 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12A···O1i | 0.93 | 2.51 | 3.311 (2) | 144 |
| Symmetry codes: (i) −x+2, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12A···O1i | 0.93 | 2.51 | 3.311 (2) | 144 |
| Symmetry codes: (i) −x+2, −y+1, −z+1. |
The authors would like to express their deep appreciation to the Start-up Fund for PhDs of the Natural Scientific Research of Zhengzhou University of Light Industry (No.2005001) and the Fund for Natural Scientific Research of Zhengzhou University of Light Industry, China (000455).
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The derivatives of pyrazoline are mostly used in medicine, for example as antitumor (Hatheway et al., 1978), analgesic (Sobczak & Pawlaczyk, 1998), and antimicrobial (Mahajan et al., 1991) agents. As part of our work, the new title compound (I) are synthesized in our group.
The pyrazoline ring assumes an envelope conformation with the furanyl-bearing carbon atom at the flap position (Fig. 1). Intermolecular weak C—H···O hydrogen bonding is present in the crystal structure. (Fig. 2 and Table 1).